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Fluorescent compound, making method, and fluorescent resin composition

a technology of fluorescent compounds and resins, applied in the field of fluorescent compounds, can solve the problems of difficult failure to improve the solubility of low polar solvents and resins such as aliphatic hydrocarbons and silicone resins, and difficulty in uniform dispersion of fluorescent compounds within resins, etc., to achieve improved compatibility with organic solvents and resins, improved purity, and easy formulation of lightness and color saturation

Active Publication Date: 2013-08-15
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent describes a fluorescent compound that can be easily dispersed in various media and used to create transparent and color-saturated resin compositions. The compound has a high purity and efficiency, and can be purified to a high level. The compound can be used in various applications such as in the creation of fluorescent resin compositions. The compound has a formula that includes specific groups, and can be used to create various ring structures. The compound also contains siloxane groups, which improve its solubility. Overall, the patent describes a new and improved fluorescent compound that is easy to use and can be used in various applications.

Problems solved by technology

However, the method of Patent Document 1 has the problem that since complete removal of unreacted fluorescent compound is difficult, it will agglomerate and precipitate during storage or service, undesirably inviting changes of the outer appearance and optical properties.
Also, the silicone resin, which is a polymeric substance, has a molecular weight distribution and is non-uniform in the chemical structure of every molecule.
It is thus difficult that the fluorescent compound is uniformly dispersed within the resin.
The method of Patent Document 3 achieves an improved solubility in organic solvents, but fails to improve the solubility in low polar solvents and resins such as aliphatic hydrocarbons and silicone resins.
It is difficult to use the relevant compounds in these solvents and resins as dye or fluorescent substance.

Method used

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  • Fluorescent compound, making method, and fluorescent resin composition
  • Fluorescent compound, making method, and fluorescent resin composition
  • Fluorescent compound, making method, and fluorescent resin composition

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 2,7-dibromo-9,9′-di-[3-(1-trimethylsiloxy-1,3,3,3-tetramethyldisiloxan-1-yl)propyl]fluorene (Compound #1)

[0092]A 100-ml three-necked flask equipped with a reflux condenser and stirrer was purged with nitrogen and charged with 845.0 mg (2.11 mmol) of 2,7-dibromo-9,9′-diallylfluorene, 15.2 mg of a 2 wt % xylene solution of platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex, and 5 ml of dry toluene. To the flask, 1.01 g (4.54 mmol) of 1,1,1,3,5,5,5-heptamethyltrisiloxane was added dropwise over 10 minutes. After the completion of dropwise addition, the reaction solution was stirred for 6 hours at room temperature. The solution was concentrated in vacuum. Water and toluene were added to the concentrate, followed by separatory operation to extract the organic layer. The resulting solution was dried over magnesium sulfate and concentrated under reduced pressure on a rotary evaporator, yielding 1.70 g of a pale yellow liquid.

[0093]On time-of-flight mass spectrometry...

example 2

Synthesis of 2,7-bis(biphenyl)-9,9′-di-[3-(1-trimethyl-siloxy-1,3,3,3-tetramethyldisiloxan-1-yl)propyl]fluorene (Compound #2)

[0096]A 100-ml three-necked flask equipped with a reflux condenser and stirrer was purged with nitrogen and charged with 1.70 g (2.00 mmol) of 2,7-dibromo-9,9′-di[3-(1-trimethylsiloxy-1,3,3,3-tetramethyldisiloxan-1-yl)propyl]-fluorene, 1.02 g (5.15 mmol) of biphenylboronic acid, 131.4 mg (0.11 mmol) of tetrakisi(triphenylphosphine), and 20 ml of dimethoxyethane. To the flask, 1.10 g (7.96 mmol) of potassium carbonate in 4 ml of water was added dropwise. After the completion of dropwise addition, the reaction solution was stirred for 4.5 hours at 67° C. Water and toluene were added to the solution, followed by separatory operation to extract the organic layer. The resulting solution was dried over magnesium sulfate, concentrated under reduced pressure on a rotary evaporator, and purified by HPLC, yielding 1.48 g of a white solid.

[0097]On NMR and MALDI-TOFMS spe...

example 3

Synthesis of 2,7-dibromo-9,9′-di-[3-(undecamethylpenta-siloxan-1-yl)propyl]fluorene (Compound #3)

[0102]A 100-ml three-necked flask equipped with a reflux condenser and stirrer was purged with nitrogen and charged with 1.33 g (3.29 mmol) of 2,7-dibromo-9,9′-diallylfluorene, 15.0 mg of a 2 wt % xylene solution of platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex, and 6 ml of dry toluene. To the flask, 3.00 g (8.09 mmol) of 1,1,3,3,5,5,7,7,9,9,9-undecamethyltrisiloxane was added dropwise over 10 minutes. After the completion of dropwise addition, the reaction solution was stirred for 7 hours at room temperature. Water and toluene were added to the solution, followed by separatory operation to extract the organic layer. The resulting solution was dried over magnesium sulfate, concentrated under reduced pressure on a rotary evaporator, and purified by silica gel chromatography, yielding 2.63 g of a pale yellow liquid.

[0103]On MALDI-TOFMS analysis, the liquid was identified to...

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Abstract

Novel fluorescent compounds having a specific structure are provided. They have improved solubility in organic solvents and compatibility even with low polar resins, especially silicone resins. Using the compounds, transparency fluorescent resin compositions are formulated. Since the fluorescent compound is a single compound, it can be purified to a high purity and has a high fluorescence efficiency.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This non-provisional application claims priority under 35 U.S.C. §119 (a) on Patent Application No. 2012-027589 filed in Japan on Feb. 10, 2012, the entire contents of which are hereby incorporated by reference.TECHNICAL FIELD[0002]This invention relates to novel fluorescent compounds, a method of preparing the same, and fluorescent resin compositions.BACKGROUND ART[0003]Organic compounds having a fluorescent chromophore (to be referred to as “fluorescent compounds”, hereinafter) are often used as fluorescent ink or pigment to offer a colorant for paper, fibers and resins partly because they are less expensive than fluorescent inorganic compounds.[0004]The colorants are generally classified into two categories, dyes and pigments. The pigment is an agglomerate of molecules having a chromophore and has a large particle size whereas the dye is a chromophore-containing molecule which is dissolvable in media including solvents and resins. In ge...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C09K11/06H10K99/00
CPCC09K11/06H01L51/0052H05B33/14C09K2211/1011C09K2211/1014C09B1/00H01L51/0054H01L51/0058H01L51/0094H01L51/5012C09B57/00C07F7/1864C07F7/1804H10K85/622H10K85/615H10K85/626H10K85/40H10K50/11C07C13/38C07D307/78C07D471/04C07F13/00C08K5/01C08L83/00H10K50/00
Inventor ITO, YUSUKEKIYOMORI, AYUMU
Owner SHIN ETSU CHEM IND CO LTD
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